Chemistry of Natural Compounds

, Volume 6, Issue 1, pp 30–34 | Cite as

Steroids

XXXVI. The opening of an epoxide ring with organometallic compounds
  • L. V. Sokolova
  • L. I. Klimova
  • Z. A. Yaroslavtseva
  • E. M. Kaminka
  • N. N. Suvorov
Article
  • 43 Downloads

Conclusions

The opening of the epoxide ring of the 3,20-diketal of 16α, 17α-epoxy-Δ5-pregnene-3, 20-dione and of the acetate of the 20-ketal of 16α, 17α-epoxy-Δ5-pregnene-3β-ol-20-one with methyllithium has been studied. It was found that no products of the nucleophilic addition of methyllithium to the epoxide ring are formed, and after deketalization, 16-methyl-Δ4,16-pregnadiene-3,20-dione, Δ4,15-pregnadiene-17α-ol-3,20-dione, 16-methyl-Δ5,16-pregnadiene-3β-ol-20-one, and Δ5,15-pregnadiene-3β,17α-diol-20-one were isolated. The formation of the latter is due to alkali-catalyzed opening of the epoxide ring in the presence of the strong base, that methyllithium is.

Keywords

Epoxide Dione Methyl Iodide Organometallic Compound Nucleophilic Addition 

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Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • L. V. Sokolova
    • 1
  • L. I. Klimova
    • 1
  • Z. A. Yaroslavtseva
    • 1
  • E. M. Kaminka
    • 1
  • N. N. Suvorov
    • 1
  1. 1.Ordzhonikidze All-Union Chemical and Pharmaceutical Scientific-Research InstituteUSSR

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